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VOLUME 7
NUMBER 4
Product Directory
Grignard and
Organozinc Reagents
rieke® highly
reactive metals
grignard reagents
organozinc halides
Dialkylmagnesium
and dialkyzinc
reagents
sigma-aldrich.com
Table of Contents
Sigma-Aldrich is committed to providing the most extensive portfolio of high-quality Grignard, organozinc, and other organometallic reagents,
and we continually expand our product listing. Within each section of this directory, products are listed by increasing carbon content.
If you are unable to find a reagent for your research “Please Bother Us” at
nwallock@sial.com, or contact your local Sigma-Aldrich office (see back cover).
Foreword
Reuben D. Rieke
President and CEO, Rieke Metals, Inc.
Professor Emeritus, University of Nebraska
Lincoln, NE
In the last 35 years, considerable research has been done in the area of generating reactive metals that can be used to synthesize novel
organometallic reagents. In 1972, we reported a general approach for preparing highly reactive metal powders, relying on the reduction of
metal salts with alkali metals in ethereal or hydrocarbon solvents. These useful metal powders were eventually named “Rieke metals” and
they have greatly expanded the number of organometallic reagents that can be made.
Grignard reagents are some of the most widely employed organometallic reagents and a wealth of information is known about their
reactivity. Although the formation of these reagents is commonly thought to be completely general, there are many organic halides that do
not react with ordinary magnesium turnings. The use of Rieke® Magnesium dramatically increases the range of Grignard reagents that are
possible by allowing reactions at lower temperatures and thus avoiding decomposition and side reactions. Rieke® Magnesium, as well as an
abundant portfolio of pre-formed Grignard reagents, are conveniently available through Sigma-Aldrich.
Prior to the discovery of Rieke® Zinc, it was not possible to react alkyl, aryl, and vinyl bromides or chlorides directly with zinc metal. The
preparation of these reagents was only possible by a metathesis reaction of a zinc halide with an organolithium or Grignard reagent.
Unfortunately, this approach was of limited utility since the process was not compatible with many types of functional groups. Rieke® Zinc,
on the other hand, will react directly with the bromides or chlorides and will tolerate a variety of sensitive groups such as nitriles, esters,
amides, ethers, sulfides, and ketones to give functionalized organozinc reagents. Organozinc reagents are powerful C–C bond-forming tools,
participating in Cu(I)-promoted reactions (developed at Rieke Metals, Inc.) or in Pd-catalyzed cross-coupling reactions, i.e. the Negishi coupling.
Sigma-Aldrich offers Rieke® Zinc, as well as numerous pre-formed Rieke® organozinc reagents for use in these and other important reactions.
R R O
ROH OH
R
Ar R
X
O R O2 O O
O RCO2H
CuX CuX
X Ar Cl
CuX CO2
Br O
O R'CN R' Br X O
R'
RMgX R' MgX R RZnX
R' R O CuX R R'
CuX
R3' SnCl
R' Y
O X Ar X
O R3' Sn R
R' R R'X [Pd]
or R' R" CuX
OH
s i g m a - a l d r i c h . c o m
R' R R
R OH Ar R
R R'
R' R"
R
Grignard Reagents
Reactive Metals
Rieke® Highly
Alkyl
O r d e r :
[41251-37-0] 1.0 M in diethyl ether: 225754, 256609 [22649-70-3]
1.0 M in diethyl ether: 293091 0.5 M in tetrahydrofuran: 419583
Butylmagnesium chloride solution
Ethylmagnesium chloride solution C4H9ClMg 3-Butenylmagnesium bromide solution
MW: 116.87 C4H7BrMg
1 . 8 0 0 . 3 2 5 . 3 0 1 0
C2H5ClMg CH3 MgCl
3.0 M in diethyl ether: 189871, 256978 2.0 M in diethyl ether: 225746 1.0 M in diethyl ether: 256021
1.0 M in tert-butyl methyl ether: 345105 2.0 M in tetrahydrofuran: 479683
1.0 M in tetrahydrofuran: 364665, 364673 (1,3-Dioxolan-2-ylmethyl)magnesium
Isobutylmagnesium bromide solution bromide solution
Propylmagnesium chloride solution C4H9BrMg C4H7BrMgO2 O
CH3
C3H7ClMg MW: 161.32 MW: 191.31
S e r v i c e :
MgBr
H3C O MgBr
MW: 102.85 H3C [926-62-5] [180675-22-3]
MgCl
[2234-82-4] 2.0 M in diethyl ether: 338257 0.5 M in tetrahydrofuran: 472611
2.0 M in diethyl ether: 224391
sec-Butylmagnesium chloride solution Pentylmagnesium chloride solution
Isopropylmagnesium chloride solution C4H9ClMg C5H11ClMg
1 . 8 0 0 . 2 3 1 . 8 3 2 7
CH3
C3H7ClMg MW: 116.87 H3C
MW: 130.90 MgCl
CH3
MW: 102.85
H3C
[15366-08-2] MgCl [6393-56-2]
MgCl
[1068-55-9] H3C
2.0 M in diethyl ether: 224421 2.0 M in tetrahydrofuran: 469033
2.0 M in diethyl ether: 224383, 257028
2.0 M in tetrahydrofuran: 230111, 257036
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
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1,1-Dimethylpropylmagnesium 2-Bromobenzylmagnesium
chloride solution bromide solution R 2-Methoxybenzylmagnesium
C5H11ClMg C7H6Br2Mg chloride solution R
MgCl MgBr
MW: 130.90 H3C MW: 274.24 C8H9ClMgO
H3C CH3 MgCl
[28276-08-6] [56812-60-3] Br MW: 180.91
OCH3
1.0 M in diethyl ether: 277282 0.25 M in diethyl ether: 562149 [480438-46-8]
0.25 M in tetrahydrofuran: 562092
2,2-Dimethylpropylmagnesium 3-Bromobenzylmagnesium
chloride solution R bromide solution R 3-Methoxybenzylmagnesium
C5H11ClMg C7H6Br2Mg MgBr chloride solution R
H3C
MW: 130.90 MgCl MW: 274.24 C8H9ClMgO
H3C CH3 MgCl
[13132-23-5] [107549-22-4] Br MW: 180.91
1.0 M in diethyl ether: 550213 0.25 M in diethyl ether: 562130 [26905-40-8]
OCH3
C6H11BrMgO2 O
C8H9ClMg 0.2 M in tetrahydrofuran: 563811
MgCl
MW: 219.36 MW: 164.92
O MgBr
[480438-44-6] [29875-05-6] CH3
Grignard Reagents
2-Methyl-2-phenylpropylmagnesium Tetradecylmagnesium chloride solution
chloride solution C14H29ClMg
C10H13ClMg H3C CH3 MW: 257.14 H3C MgCl
MgCl
MW: 192.97 [110220-87-6]
[35293-35-7] 1.0 M in tetrahydrofuran: 337781
0.5 M in diethyl ether: 420204
Alkenyl
O r d e r :
Alkynyl
1 . 8 0 0 . 3 2 5 . 3 0 1 0
MW: 84.79 MgCl MW: 143.26 H3C MgBr C8H5BrMg
[65032-27-1] [16466-97-0] MW: 205.33 MgBr
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Aryl
MgBr
1.0 M in tetrahydrofuran: 331376 MW: 199.30 [480438-47-9] Cl CH3
MW: 217.29
0.5 M in tetrahydrofuran: 561738
3,4-Dichlorophenylmagnesium [62351-47-7] F
bromide solution R 0.5 M in tetrahydrofuran: 561029 5-Fluoro-2-methylphenyl-
C6H3BrCl2Mg MgBr
magnesium bromide solution R
MW: 250.20 3,4,5-Trifluorophenylmagnesium
Cl C7H6BrFMg
[79175-35-2] F MgBr
Cl bromide solution R MW: 213.33
0.5 M in tetrahydrofuran: 562270 C6H2BrF3Mg F MgBr [186496-59-3] CH3
MW: 235.28
F 0.5 M in tetrahydrofuran: 561746
3,5-Dichlorophenylmagnesium [156006-28-9] F
bromide solution R 0.3 M in tetrahydrofuran: 561797 4-Fluoro-3-methylphenyl-
C6H3BrCl2Mg Cl MgBr
magnesium bromide solution
MW: 250.20 Pentafluorophenylmagnesium C7H6BrFMg MgBr
[82297-90-3] bromide solution
Cl MW: 213.33
F
0.5 M in tetrahydrofuran: 562289 C6BrF5Mg F [82297-89-0] CH3
MW: 271.27 F MgBr
1.0 M in tetrahydrofuran: 344605
[879-05-0]
3-Chloro-4-fluorophenyl- F F
F
magnesium bromide solution R 3-Fluoro-4-methylphenyl-
C6H3BrClFMg 0.5 M in diethyl ether: 442585
MgBr
magnesium bromide solution R
MW: 233.75 C7H6BrFMg MgBr
F
[413589-34-1]
Cl
o-Tolylmagnesium chloride solution MW: 213.33
C7H7ClMg MgCl [185077-02-5]
H3C
0.5 M in tetrahydrofuran: 563676 F
MW: 150.89
[33872-80-9] CH3 0.5 M in tetrahydrofuran: 561711
3-Chloro-5-fluorophenyl-
magnesium bromide solution 1.0 M in tetrahydrofuran: 360023
2-Methoxyphenylmagnesium
C6H3BrClFMg F MgBr bromide solution
MW: 233.75 o-Tolylmagnesium bromide solution C7H7BrMgO MgBr
[480438-50-4] C7H7BrMg MgBr MW: 211.34
Cl
MW: 195.34 [16750-63-3] OCH3
0.5 M in tetrahydrofuran: 563390
[932-31-0] CH3
1.0 M in diethyl ether: 662453
2.0 M in diethyl ether: 298980 1.0 M in tetrahydrofuran: 470414
4-Chloro-3-fluorophenyl-
magnesium bromide solution R
s i g m a - a l d r i c h . c o m
Grignard Reagents
(50:50): 512931
3,5-Bis(trifluoromethyl)phenyl- 4-n-Propylphenylmagnesium
5-Fluoro-2-methoxyphenyl- magnesium bromide solution bromide solution R
magnesium bromide solution R C8H3BrF6Mg F3C MgBr C9H11BrMg MgBr
C7H6BrFMgO F MgBr MW: 317.31 MW: 223.39
MW: 229.33 [112981-69-8] [87942-08-3] H3C
CF3
[188132-02-7] OCH3
4-Ethylphenylmagnesium 4-Isopropylphenylmagnesium
3-Fluoro-4-methoxyphenyl-
bromide solution R bromide solution R
magnesium bromide solution R
C8H9BrMg C9H11BrMg MgBr
C7H6BrFMgO MgBr MgBr
MW: 209.37 MW: 223.39 H3C
MW: 229.33 H3C
[112780-67-3]
H3CO [22873-28-5] CH3
F
0.5 M in tetrahydrofuran: 561754 0.5 M in tetrahydrofuran: 635669
0.5 M in tetrahydrofuran: 563706
4-Methoxy-2-methylphenyl- 3,5-Dimethyl-4-methoxyphenyl-
4-Thioanisolemagnesium
magnesium bromide solution R magnesium bromide solution R
bromide solution R
C8H9BrMgO C9H11BrMgO H3C MgBr
C7H7BrMgS MgBr
MgBr
MW: 225.37 MW: 239.39
MW: 227.40 H3CO
H3CS [148706-30-3] H3CO CH3 [185416-17-5]
[18620-04-7] CH3
O r d e r :
bromide solution R
bromide solution R bromide solution
C8H9BrMg MgBr C8H9BrMgO2 MgBr C10H13BrMg MgBr
[134640-85-0]
CH3 [138109-49-6] H3CO OCH3 [63488-10-8] H3C
CH3
CH3
0.5 M in tetrahydrofuran: 562025
1 . 8 0 0 . 3 2 5 . 3 0 1 0
0.5 M in tetrahydrofuran: 563757 2.0 M in diethyl ether: 324655
2,5-Dimethoxyphenylmagnesium 1-Naphthylmagnesium
2,4-Dimethylphenylmagnesium
bromide solution R bromide solution R
bromide solution R
C8H9BrMgO2 H3CO MgBr C10H7BrMg MgBr
C8H9BrMg MgBr
MW: 241.36 MW: 231.37
MW: 209.37
[62890-98-6] OCH3
[703-55-9]
[34589-46-3] H3C CH3
0.5 M in tetrahydrofuran: 561819 0.25 M slurry in tetrahydrofuran: 561673
0.5 M in tetrahydrofuran: 562041
3,4-Dimethoxyphenylmagnesium 2-Naphthylmagnesium
2,5-Dimethylphenylmagnesium
Te c h n i c a l
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[3-(1-Pyrrolidinylmethyl)phenyl]- 4-Benzyloxyphenylmagnesium 8
4-Phenoxyphenylmagnesium bromide solution
magnesium bromide solution R
bromide solution R
C13H11BrMgO
C11H14BrMgN MgBr
C12H9BrMgO MW: 287.43 MgBr
MW: 264.44 MgBr
MW: 273.41 [120186-59-6]
[480424-79-1]
N [21473-02-9] O O
1.0 M in tetrahydrofuran: 672998
0.5 M in tetrahydrofuran: 561681
0.25 M in tetrahydrofuran: 571180
9-Phenanthrylmagnesium
3-[Bis(trimethylsilyl)amino]phenyl-
[4-(1-Pyrrolidinylmethyl)phenyl]- bromide solution R
magnesium chloride solution
magnesium bromide solution R C14H9BrMg MgBr
C12H22ClMgNSi2 MgCl
C11H14BrMgN MW: 281.43
MgBr MW: 296.24
MW: 264.44 [71112-64-6]
N [174484-84-5] N
[480424-78-0] (H3C)3Si Si(CH3)3
0.5 M in tetrahydrofuran: 563749
0.25 M in tetrahydrofuran: 571172 1.0 M in tetrahydrofuran: 372005
3-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl-
[2-(4-Morpholinylmethyl)phenyl]- [2-(1-Piperidinylmethyl)phenyl]- methyl)phenylmagnesium bromide
magnesium bromide solution R magnesium bromide solution R solution R
C11H14BrMgNO MgBr
C12H16BrMgN MgBr C14H18BrMgNO2 MgBr
N
MW: 280.44 O MW: 278.47 MW: 336.51 O
N N
[480424-77-9] [480424-81-5] O
Heteroaryl
Organozinc Halides
Organozinc Halides
Alkyl
O r d e r :
0.5 M in tetrahydrofuran: 680966 0.5 M in tetrahydrofuran: 499072
Pentylzinc bromide solution R
2-Cyanoethylzinc bromide solution R C5H11BrZn 4-Cyanobutylzinc bromide solution R
C3H4BrNZn MW: 216.43 H3C
ZnBr C5H8BrNZn
1 . 8 0 0 . 3 2 5 . 3 0 1 0
MW: 199.36 NC
ZnBr [308796-10-3] MW: 227.42 NC
ZnBr
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10
ZnBr
H3C O
MW: 246.42 H3CO ZnBr [62673-31-8]
[312693-18-8] CH3
0.5 M in tetrahydrofuran: 630403 0.5 M in tetrahydrofuran: 497517
0.5 M in tetrahydrofuran: 498815
Heptylzinc bromide solution R 2-Fluorobenzylzinc
Hexylzinc bromide solution R C7H15BrZn chloride solution R
C6H13BrZn MW: 244.49 H3C
ZnBr C7H6ClFZn
ZnCl
MW: 230.46 H3C ZnBr [7608-06-2] MW: 209.96
[124397-96-2] 0.5 M in tetrahydrofuran: 533270 [312693-05-3] F
H2C
[226570-65-6] C7H12BrNZn 2-Bromobenzylzinc bromide solution R
0.5 M in tetrahydrofuran: 498734 MW: 255.47 NC
ZnBr C7H6Br2Zn
ZnBr
[312624-28-5] MW: 315.32
0.5 M in tetrahydrofuran: 497924 [307496-27-1] Br
Organozinc Halides
ZnBr
ZnCl
MW: 272.41 MW: 206.00
[308796-30-7] [312693-19-9] CH3
2-Iodobenzylzinc bromide solution R F
O r d e r :
2,4-Difluorobenzylzinc
bromide solution R C7H2ClF5Zn F C8H6ClF3Zn ZnCl
F
C7H5BrF2Zn MW: 281.93 ZnCl MW: 259.97
MW: 272.41 ZnBr [308796-02-3] F F [480438-42-4] CF3
F
[307496-26-0] F F 0.5 M in tetrahydrofuran: 561045
1 . 8 0 0 . 3 2 5 . 3 0 1 0
0.5 M in tetrahydrofuran: 499064
0.5 M in tetrahydrofuran: 520306
2-Methoxybenzylzinc
2,3,4,5,6-Pentafluorobenzylzinc chloride solution R
2,5-Difluorobenzylzinc
bromide solution R C8H9ClOZn
chloride solution R
C7H2BrF5Zn F ZnCl
C7H5ClF2Zn MW: 222.00
F
F
ZnCl MW: 326.38 ZnBr [312693-15-5] OCH3
MW: 227.95
[352534-75-9] F F
[312692-89-0] F 0.5 M in tetrahydrofuran: 498785
F
0.5 M in tetrahydrofuran: 498092 0.5 M in tetrahydrofuran: 541273
3-Methoxybenzylzinc
Te c h n i c a l
4-Methoxybenzylzinc
5-Cyano-5-methylhexylzinc
2,6-Difluorobenzylzinc chloride solution R
bromide solution R
bromide solution R C8H9ClOZn
C8H14BrNZn ZnCl
C7H5BrF2Zn F H3C CH3 MW: 222.00
MW: 269.50 H3CO
MW: 272.41 NC ZnBr [312693-17-7]
ZnBr [312693-22-4]
[307496-33-9] 0.5 M in tetrahydrofuran: 498807
1 . 8 0 0 . 2 3 1 . 8 3 2 7
F
0.5 M in tetrahydrofuran: 498920
0.5 M in tetrahydrofuran: 521671
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12
CN
Alkenyl
Aryl
Organozinc Halides
[186000-41-9] F
iodide solution R iodide solution R
0.5 M in tetrahydrofuran: 533513 C6H3BrFIZn ZnI
C7H7IZn ZnI
O r d e r :
0.5 M in tetrahydrofuran: 499803
2,3-Dichlorophenylzinc 3-Fluoro-4-methylphenylzinc
3-Chlorophenylzinc iodide solution R iodide solution R iodide solution R
C6H4ClIZn ZnI C6H3Cl2IZn ZnI C7H6FIZn ZnI
1 . 8 0 0 . 3 2 5 . 3 0 1 0
Cl H3C
[186000-42-0] [307531-97-1] Cl
[312693-08-6] F
Cl
0.5 M in tetrahydrofuran: 497827 0.5 M in tetrahydrofuran: 535214 0.5 M in tetrahydrofuran: 498610
Cl
[312692-85-6] Cl
[288309-53-5] CN
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14
ZnI
ZnI
MW: 299.42 MW: 297.45 MW: 341.46
[300825-30-3] OCH3 [282727-21-3] CH3 [282727-18-8]
O O CH3
0.5 M in tetrahydrofuran: 498831 0.5 M in tetrahydrofuran: 498408
0.5 M in tetrahydrofuran: 498467
4-Methoxyphenylzinc 3,4-Dimethylphenylzinc
iodide solution R iodide solution R 4-(Ethoxycarbonyl)phenylzinc
C7H7IOZn ZnI C8H9IZn ZnI bromide solution R
MW: 299.42 MW: 297.45 C9H9BrO2Zn ZnBr
H3C
[254454-47-2] H3CO [312692-97-0] H3C
MW: 294.46 H3C O
[131379-15-2]
0.5 M in tetrahydrofuran: 498858 0.5 M in tetrahydrofuran: 498416 O
[312692-94-7]
CH3 iodide solution R
H3C
C9H11IZn ZnI
0.5 M in tetrahydrofuran: 498378 MW: 311.48 CH3
[308796-17-0] CH3
Heteroaryl
[352530-36-0] Cl N
O r d e r :
bromide solution R
C4H2BrClSZn C6H6BrNZn CH3
MW: 262.87 Cl ZnBr MW: 237.41
S
[312624-22-9] [308795-91-7] N ZnBr
1 . 8 0 0 . 3 2 5 . 3 0 1 0
Dialkylmagnesium and Dialkylzinc Reagents
Di-n-butylmagnesium solution Diethylzinc solution Dibutylzinc solution
C8H18Mg C4H10Zn C8H18Zn
MW: 138.53 H3C Mg CH3 MW: 123.51 H3C Zn CH3 MW: 179.62 H3C Zn CH3
[1191-47-5] [557-20-0] [1119-90-0]
Te c h n i c a l
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